JPH0249299B2 - - Google Patents
Info
- Publication number
- JPH0249299B2 JPH0249299B2 JP56072842A JP7284281A JPH0249299B2 JP H0249299 B2 JPH0249299 B2 JP H0249299B2 JP 56072842 A JP56072842 A JP 56072842A JP 7284281 A JP7284281 A JP 7284281A JP H0249299 B2 JPH0249299 B2 JP H0249299B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- condensate
- mol
- diamide
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 23
- 239000000194 fatty acid Substances 0.000 claims abstract description 23
- 229930195729 fatty acid Natural products 0.000 claims abstract description 23
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 22
- 239000002280 amphoteric surfactant Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 11
- 238000003860 storage Methods 0.000 claims abstract description 10
- 239000000047 product Substances 0.000 claims description 23
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 230000029936 alkylation Effects 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000007859 condensation product Substances 0.000 abstract 3
- 230000002152 alkylating effect Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- BZQIOJCTHFYLNC-UHFFFAOYSA-N 1-chloro-1-hydroxypropane-1-sulfonic acid Chemical compound CCC(O)(Cl)S(O)(=O)=O BZQIOJCTHFYLNC-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 description 3
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000004420 diamide group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 125000003142 tertiary amide group Chemical group 0.000 description 1
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
Abstract
Description
【発明の詳細な説明】
本発明は、アミノアルキルアルカノールアミン
と脂肪酸との粗縮合物を精製することを含んで成
る貯蔵安定性の高い両性界面活性剤の製法に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a process for producing a storage-stable amphoteric surfactant comprising purifying a crude condensate of an aminoalkyl alkanolamine and a fatty acid.
両性界面活性剤の重要な製法はＮ−モノ置換ア
ルキレンジアミン縮合物を基礎にしており、該化
合物はさらにアルキル化剤、たとえばクロロ酢酸
ナトリウムとの反応によりアルキル化される。Ｎ
−アミノエチルエタノールアミンおよび脂肪酸を
基礎とする化合物は皮膚に温和な界面活性剤とし
て重要である。 An important method for the preparation of amphoteric surfactants is based on N-monosubstituted alkylene diamine condensates, which are further alkylated by reaction with alkylating agents, such as sodium chloroacetate. N
- Compounds based on aminoethylethanolamine and fatty acids are important as skin-friendly surfactants.
この様な化合物の製法は、基本的には米国特許
第2528378号、第2528379号および第2528380号に
開示されている。従来は、この様な反応ではイミ
ダゾリンのアルキル化または第四級化化合物が生
成していると推測されていたが、現在では、水性
媒体中でのイミダゾリン−中間段階の加水分解に
より生成するアミノアミドのアルキル化または第
四級化化合物が特に重要であることが示されてい
る（たとえばDE−AS1084414参照）。 The preparation of such compounds is essentially disclosed in US Pat. Nos. 2,528,378, 2,528,379 and 2,528,380. Previously, it was assumed that such reactions produced alkylated or quaternized compounds of the imidazoline, but it is now believed that the imidazoline-intermediate hydrolysis in an aqueous medium produces aminoamides. Alkylated or quaternized compounds have been shown to be of particular interest (see for example DE-AS 1084414).
この様な界面活性剤の製造は基本的に次の様に
して行われる。すなわち、脂肪酸または脂肪酸混
合物約１モルおよびアミノアルキルアルカノール
アミン、特にアミノエチルエタノールアミン１モ
ルを、次第に温度を高め、最後には減圧にして縮
合させる。次いで、該縮合物を通常アルカリ水溶
液中、可変量のアルキル化剤、たとえばクロロ酢
酸ナトリウムにより両性界面活性剤に変換する。
反応工程の詳細は、これまでに引用した文献、さ
らに
Dr.K.Lindner“Tenside−Textilhilfsmittel−
Waschrohstoffe”Wissenschaftliche Verlags
GmbH、Stuttgart 1964、1041／1042頁およびこ
れに引用された原文献、たとえばDE−
OS2752116、ヨーロツパ特許出願公開001006なら
びに米国特許第2773068号ならびに第3408361号に
記載されている。 The production of such a surfactant is basically carried out as follows. That is, approximately 1 mol of a fatty acid or fatty acid mixture and 1 mol of an aminoalkylalkanolamine, in particular aminoethylethanolamine, are condensed at progressively higher temperatures and finally under reduced pressure. The condensate is then converted to an amphoteric surfactant with variable amounts of an alkylating agent, such as sodium chloroacetate, usually in aqueous alkaline solution.
Details of the reaction process can be found in the literature cited so far, as well as in Dr. K. Lindner “Tenside-Textilhilfsmittel-
Waschrohstoffe”Wissenschaftliche Verlags
GmbH, Stuttgart 1964, pages 1041/1042 and the original documents cited therein, e.g.
OS2752116, European Patent Application Publication No. 001006 and US Patent Nos. 2,773,068 and 3,408,361.
得られた両性界面活性剤の品質、特に貯蔵安定
性は、最初の縮合段階で生成するイミダゾリン誘
導体の純度により大きく左右される。脂肪酸とア
ミノアルキルアルカノールアミンとの反応は所望
のイミダゾリン誘導体が生成する方向に進むだけ
でなく、更に副反応は反応発生を一層複雑にす
る。この様な現象の重要性は最近になつて改めて
明らかにされた〔E.G.Lomax“New and
improved balanced amphoterics”、
Manufacturing Chemist and Aerosol News、
第50巻第８号1979年８月第39〜41頁参照〕。たと
えば次の様に記述されている：イミダゾリン生成
工程においてアミノエチルエタノールアミンを過
剰に加えることにより望ましくない副反応を抑制
することができるが、過剰部分は反応終了時に留
去しなければならない。けれども過剰のアミノエ
チルエタールアミンはその時点で環化してピペラ
ジンになり、新たな障害を引き起こす。最初の反
応工程で得られるイミダゾリンの純度は、後続の
アルキル化により得られる両性界面活性剤または
その水溶液の貯蔵安定性に重大な影響を有してい
る。また、簡単な精製だけでは短期または長期の
貯蔵後に、濁りまたは沈殿という形で固相の分離
をもたらす。この様な生成物は実用に際しては役
に立たないかまたは少くとも限定された価値しか
ない。 The quality, especially the storage stability, of the obtained amphoteric surfactants is largely determined by the purity of the imidazoline derivative formed in the first condensation step. The reaction of the fatty acid with the aminoalkyl alkanolamine not only proceeds towards the formation of the desired imidazoline derivative, but also side reactions further complicate the reaction occurrence. The importance of this phenomenon has recently been made clear again [EGLomax “New and
improved balanced amphoteric
Manufacturing Chemist and Aerosol News,
See Vol. 50, No. 8, August 1979, pp. 39-41]. For example, it is stated as follows: Undesirable side reactions can be suppressed by adding an excess of aminoethylethanolamine in the imidazoline production process, but the excess must be distilled off at the end of the reaction. However, the excess aminoethylethalamine then cyclizes to piperazine, creating a new problem. The purity of the imidazoline obtained in the first reaction step has a significant influence on the storage stability of the amphoteric surfactant or its aqueous solution obtained by subsequent alkylation. Also, simple purification results in separation of the solid phase in the form of turbidity or precipitation after short or long-term storage. Such products are of no practical use, or at least of limited value.
本発明は、前述の種類の両性界面活性剤の製造
における改良、特に両性界面活性剤の貯蔵安定性
の向上を目的とする改良に向けられたものであ
る。 The present invention is directed to improvements in the production of amphoteric surfactants of the type mentioned above, in particular improvements aimed at improving the storage stability of amphoteric surfactants.
本発明は、最初に得られるアミノアルキルアル
カノールアミンと脂肪酸との縮合物に簡単な精製
工程を導入して、存在する不要の副生成物を非常
に簡単に除去する。従つて本発明は、最初の工程
でできるだけ純粋な縮合物を調整する為に従来行
われてきた不経済な余分な手順を不必要にしよう
というものである。 The present invention introduces a simple purification step to the initially obtained condensate of aminoalkyl alkanolamine and fatty acid, which very easily removes any unwanted by-products present. The invention therefore seeks to obviate the need for the uneconomical extra steps traditionally carried out in order to prepare as pure a condensate as possible in the first step.
本発明は、簡単なアルカリ加水分解により、脂
肪酸とアミノアルキルアルカノールアミンとの粗
縮合物を精製品に変換することができ、後続のア
ルキル化および要すれば第四級化により特に貯蔵
安定性の優れた改良された両性界面活性剤が得ら
れるという驚くべき事実を見い出したことに基づ
いている。 The present invention makes it possible to convert crude condensates of fatty acids and aminoalkyl alkanolamines into purified products by simple alkaline hydrolysis, with subsequent alkylation and optionally quaternization providing particularly storage-stable properties. It is based on the surprising discovery that superior and improved amphoteric surfactants are obtained.
本発明の要旨は、一般式：
H2N−（CH2）n−NH−（CH2）o−OH
［式中、ｍは２〜６、およびｎは２または３の数
を表わす。］
で示されるアミノアルキルアルカノールアミンと
炭素数６〜22の脂肪酸との粗縮合物を精製し、次
いで、精製された縮合物を続いてアルキル化およ
び好ましくは第四級化して貯蔵安定性の高い両性
界面活性剤を製造する方法において、脂肪酸とア
ミノアルキルアルカノールアミンとの粗縮合物を
アルカリ加水分解に付することを特徴とする方法
に存する。 The gist of the present invention is the general formula: H2N- ( CH2 ) n -NH-( CH2 ) o -OH [wherein m represents a number of 2 to 6, and n represents a number of 2 or 3]. ] A crude condensate of an aminoalkyl alkanolamine represented by the formula and a fatty acid having 6 to 22 carbon atoms is purified, and the purified condensate is subsequently alkylated and preferably quaternized to obtain a product with high storage stability. A method for producing an amphoteric surfactant, characterized by subjecting a crude condensate of a fatty acid and an aminoalkyl alkanolamine to alkaline hydrolysis.
本発明方法において、アルカリ加水分解に際し
て加えるアルカリ量は、粗縮合物中に存在する一
般式：
で示されるジアミドの量に応じて調節するのが有
利である。この場合、該工程中のアルカリ量は、
粗縮合物中のジアミドに対して少くともほぼ等モ
ル量になる様にするのが特に好ましい。 In the method of the present invention, the amount of alkali added during alkaline hydrolysis is determined by the general formula present in the crude condensate: Advantageously, the amount of diamide is adjusted according to the amount of diamide. In this case, the amount of alkali in the process is
It is particularly preferred that the amount is at least approximately equimolar to the diamide in the crude condensate.
本発明は、脂肪酸／アミン縮合物を、更にアル
キル化剤と反応させる前に、水性媒体中でアルカ
リ前処理すれば、得られる界面活性剤中の不要副
成生物の含量を著しく減少させることができると
いう事実に基づいている。実験により示される様
に、特に反応進行中に形成されたジアミドは、水
性アルカリ液中で第３級アミド基を経て定量的に
第１級アミノ基のモノアミドと脂肪酸に分解され
る。脂肪酸は、本発明の精製処理において石けん
となるが、これは反応混合物中に残留させておく
ことができる。 The present invention provides that an alkaline pretreatment of the fatty acid/amine condensate in an aqueous medium before further reaction with an alkylating agent can significantly reduce the content of unwanted by-products in the resulting surfactant. It is based on the fact that it can be done. As shown by experiments, in particular the diamide formed during the course of the reaction is quantitatively decomposed via the tertiary amide group into the monoamide of the primary amino group and the fatty acid in the aqueous alkaline solution. The fatty acids, which become soaps in the purification process of the present invention, can remain in the reaction mixture.
実際非常に驚くべきことに、最終工程で得られ
る両性界面活性剤の貯蔵安定性に関する問題点を
解決する為に従来は比較的高価な精製手段が用い
られてきたが、これは本発明の中間処理により解
決された。ここで次の点に考慮しなければならな
い。すなわち、最初の工程で得られる反応生成物
の、たとえばクロロ酢酸ナトリウムによるアルキ
ル化および要すれば第四級化は水性アルカリ性媒
体中で行われ、その際温度およびアルカリ度に関
する反応条件は、本発明の中間処理の条件に少く
とも対応する条件が選ばれるということである。
最初の工程で得られた縮合物を予め別にアルカリ
加水分解する本発明の方法が、縮合物のアルキル
化または第四級化の進行に適した水性アルカリ性
処理としてより良い結果をもたらすことができる
ということは予期されていなかつた。しかし、本
発明のアルカリ前処理により、希釈した後に６月
以上も透明さを持続する生成物が得られたのであ
る。従つて、過剰アミンの回収またはイミダゾリ
ンの蒸留という様な高価な精製方法は必要でなく
なつた。 Indeed, it is quite surprising that relatively expensive purification measures have been used in the past to overcome the storage stability problems of the amphoteric surfactants obtained in the final step; Resolved by processing. Here, the following points must be considered. That is, the alkylation and optional quaternization of the reaction product obtained in the first step, for example with sodium chloroacetate, is carried out in an aqueous alkaline medium, the reaction conditions with respect to temperature and alkalinity being adjusted according to the invention. This means that conditions that at least correspond to the intermediate processing conditions are selected.
It is believed that the process of the invention, in which the condensate obtained in the first step is previously subjected to separate alkaline hydrolysis, can give better results as an aqueous alkaline treatment suitable for proceeding with the alkylation or quaternization of the condensate. That was not expected. However, the alkaline pretreatment of the present invention resulted in a product that remained clear for more than six months after dilution. Therefore, expensive purification methods such as excess amine recovery or imidazoline distillation are no longer necessary.
本発明のアルカリ加水分解処理は、好ましくは
約70〜100℃、特に80〜90℃の温度で行う。アル
カリとしては、アルカリ金属水酸化物、就中水酸
化ナトリウムが適当である。アルカリ使用量は、
粗縮合物に含まれるジアミドに対して等モル量の
約１〜３倍の範囲が好ましい。特にジアミドに対
して１〜２当量の範囲のアルカリ量で行うのが望
ましい。粗縮合物は、本発明のアルカリ加水分解
に際して該粗縮合物の0.5〜10倍、特に１〜５倍
量の水に分散させるのが好ましい。水性アルカリ
加水分解は、副生成物として存在するジアミドが
完全に除去されるまで行う。粗生成物中のジアミ
ド含量およびその減少は、既知の方法、たとえば
イオン交換体を用いた方法により決定することが
できる。 The alkaline hydrolysis treatment of the present invention is preferably carried out at a temperature of about 70-100°C, especially 80-90°C. Suitable alkalis are alkali metal hydroxides, especially sodium hydroxide. The amount of alkali used is
The amount is preferably about 1 to 3 times the equimolar amount to the diamide contained in the crude condensate. In particular, it is desirable to use an alkali amount in the range of 1 to 2 equivalents relative to the diamide. The crude condensate is preferably dispersed in water in an amount of 0.5 to 10 times, particularly 1 to 5 times, the amount of the crude condensate during the alkaline hydrolysis of the present invention. Aqueous alkaline hydrolysis is carried out until the diamide present as a by-product is completely removed. The diamide content and its reduction in the crude product can be determined by known methods, for example using ion exchangers.
一般式：
H2N−（CH2）n−NH−（CH2）o−OH
で示されるアミノアルキルアルカノールアミンと
してはｍが２〜６およびｎが２または３である化
合物が挙げられる。特に、ｍは２、３または６が
好ましく、ｎは２が好ましい。本発明において実
施上重要な原料アミンはアミノエチルエタノール
アミンである。 Aminoalkylalkanolamines represented by the general formula: H2N- ( CH2 ) n -NH-( CH2 ) o -OH include compounds in which m is 2 to 6 and n is 2 or 3. In particular, m is preferably 2, 3 or 6, and n is preferably 2. An important raw material amine in the present invention is aminoethylethanolamine.
縮合に際して同時に用いられる脂肪酸は、炭素
数６〜22、特に炭素数８〜18のものが好ましい。
カルボン酸は、純成分または混合物として存在す
る。これらは天然のものでも合成のものでもよ
い。 The fatty acid used at the same time during the condensation preferably has 6 to 22 carbon atoms, particularly preferably 8 to 18 carbon atoms.
Carboxylic acids exist as pure components or as mixtures. These may be natural or synthetic.
本発明の主旨に従いアルカリ加水分解処理され
た縮合物は、次に自体既知の方法により両性界面
活性剤に変換される。ここでも、引用しうる膨大
な範囲の報文がこの技術に関連している。さら
に、本発明の前処理は、単にいわゆるイミダゾリ
ニウム界面活性剤の製造にとつて重要であるばか
りでなく種々応用できることが示される。アルカ
リ処理したアミン縮合物をクロルヒドロキシプロ
パンスルホン酸型のアルキル化剤、プロパンスル
ホン型のアルキル化剤、並びに後続のケン化を伴
うアクリル酸やアクリル酸エステルのようなビニ
ル化合物を用いるアルキル化におけるアルキル化
剤および２−アクリルアミド−２−メチルプロパ
ンスルホン酸または対応するアルカリ塩と反応さ
せることによつて貯蔵安定性のよい透明生成物が
得られる。 The condensate which has been subjected to alkaline hydrolysis according to the subject matter of the invention is then converted into an amphoteric surfactant by methods known per se. Again, a vast range of papers that can be cited relate to this technology. Furthermore, it is shown that the pretreatment of the present invention is not only important for the production of so-called imidazolinium surfactants, but also has various applications. Alkylation of alkali-treated amine condensates with alkylating agents of the chlorohydroxypropanesulfonic acid type, propanesulfone type, and vinyl compounds such as acrylic acid and acrylic esters with subsequent saponification By reacting with a curing agent and 2-acrylamido-2-methylpropanesulfonic acid or the corresponding alkali salt, a transparent product with good storage stability is obtained.
両性界面活性剤は、第２の反応段階における反
応の構造および程度に応じてアルキル化および場
合により第四級化された窒素を示す。さらに本発
明は、前述のアルカリ加水分解により処理された
縮合中間体を用いたこの様な両性界面活性剤の製
造も実施形態として包含している。 Amphoteric surfactants exhibit alkylated and optionally quaternized nitrogen, depending on the structure and extent of the reaction in the second reaction step. Furthermore, the present invention includes, as an embodiment, the production of such an amphoteric surfactant using the condensation intermediate treated by the above-mentioned alkaline hydrolysis.
次に実施例を示し、本発明を詳しく説明する。
実施例中、％とあるのは重量％を表わす。ジアミ
ド含量は次の様にして測定した。すなわち、縮合
物をアルコール溶液として強酸によるイオン交換
に付す。抽出物を蒸発乾固し、残渣を秤量する。
S.Z.（Sauerzahl）および全窒素を測定することに
よりジアミド量を算出することができる。 Next, examples will be shown to explain the present invention in detail.
In the examples, % represents weight %. The diamide content was measured as follows. That is, the condensate is subjected to ion exchange with a strong acid as an alcohol solution. Evaporate the extract to dryness and weigh the residue.
The amount of diamide can be calculated by measuring SZ (Sauerzahl) and total nitrogen.
実施例 １
脂肪酸とアミノエチルエタノールアミンの縮合
物の製造：−
1.1 モル比１：１
撹拌機、窒素導入管、温度計および蒸留管を
備えた三ツ口フラスコ中で、C8／18ヤシ油脂
肪酸208ｇ（１モル）とアミノエチルエタノー
ルアミン104ｇ（１モル）を混合し、ゆつくり
200℃に加熱する。加熱は約６時間続ける。ア
ミンを含む水を総量で20ｇ蒸留した後、徐々に
凝固する黄色の物質約290ｇを得た。この物質
は次の物性値を有していた。Example 1 Preparation of condensate of fatty acid and aminoethylethanolamine: - 1.1 molar ratio 1:1 In a three-neck flask equipped with a stirrer, nitrogen inlet tube, thermometer and distillation tube, 208 g of C8/18 coconut oil fatty acid ( 1 mole) and aminoethylethanolamine (104 g (1 mole)) and boiled
Heat to 200℃. Heating continues for about 6 hours. After distilling a total of 20 g of amine-containing water, approximately 290 g of a yellow substance which gradually solidified was obtained. This material had the following physical properties.
S.Z. 2.8
Nkj 9.5％
Ntitr. 4.7％
ジアミド含量（イオン交換により測定）16.1
％（＝0.04Mol／100ｇ）．230mmのUVスペクト
ル分析によればイミダゾリン含量は8.0％であ
つた。SZ 2.8 Nkj 9.5% Ntitr. 4.7% Diamide content (determined by ion exchange) 16.1
% (=0.04Mol/100g). According to UV spectrum analysis at 230 mm, the imidazoline content was 8.0%.
1.2 モル比１：1.1
1.1に記載の方法と同様にしてヤシ油脂肪酸
208ｇ（１モル）とアミノエチルエタノールア
ミン114.5ｇ（1.1モル）を縮合させた。1.2 Molar ratio 1:1.1 Coconut oil fatty acid in the same manner as described in 1.1
208 g (1 mole) and 114.5 g (1.1 mole) of aminoethylethanolamine were condensed.
徐々に凝固する黄色の物質約300ｇを得た。
これは次の物性値を有していた。 Approximately 300 g of a yellow substance was obtained which gradually solidified.
This had the following physical properties.
S.Z. 2.3
Nkj 10.2％
Ntitr 5.6％
ジアミド含量10.7％（0.02モル／100ｇ）
イミダゾリン含量3.0％
1.3 モル比１：1.5
1.1に記載の方法と同様にしてヤシ油脂肪酸
208ｇ（１モル）とアミノエチルエタノールア
ミン156ｇ（1.5モル）を縮合させた。反応中、
遊離アミン含有量をできるだけ高く保つた。反
応温度は180℃を越えず、最終圧力は約14mbar
であつた。過剰のアミンを留去して次の物性値
を有する残渣約270ｇを得た。SZ 2.3 Nkj 10.2% Ntitr 5.6% Diamide content 10.7% (0.02 mol/100g) Imidazoline content 3.0% 1.3 Molar ratio 1:1.5 Coconut oil fatty acid in the same manner as described in 1.1
208 g (1 mole) and 156 g (1.5 mole) of aminoethylethanolamine were condensed. During the reaction,
Free amine content was kept as high as possible. The reaction temperature does not exceed 180℃ and the final pressure is about 14mbar
It was hot. Excess amine was distilled off to obtain about 270 g of a residue having the following physical properties.
Nkj 10.3％
Ntitr 5.2％
ジアミド含量2.7％（＝0.006モル／100ｇ）
イミダゾリン含量96％
実施例 ２
クロル酢酸ナトリウムとの反応
2.1 アルカリ前処理無し
2.1.1
実施例1.1で得た生成物90ｇ（0.3モル、
Ntitrから算出）を水148ｇに分散させ、新た
に調製した40％クロル酢酸ナトリウム溶液
203ｇ（0.7モル）を60℃で混合する。50％苛
性ソーダ溶液56ｇ（0.7モル）を加えてPHを
11.52に調節する。この温度で２時間撹拌し、
次いで80℃で１時間加温する。PHは徐々に約
10まで低下する。濃度約40％の生成物は室温
で２日後に濁り始めた。Nkj 10.3% Ntitr 5.2% Diamide content 2.7% (=0.006 mol/100 g) Imidazoline content 96% Example 2 Reaction with sodium chloroacetate 2.1 No alkaline pretreatment 2.1.1 90 g (0.3 mol) of the product obtained in Example 1.1 ,
Freshly prepared 40% sodium chloroacetate solution by dispersing (calculated from Ntitr) in 148 g of water.
203 g (0.7 mol) are mixed at 60°C. Add 56 g (0.7 mol) of 50% caustic soda solution to adjust the pH.
Adjust to 11.52. Stir at this temperature for 2 hours,
Then, heat at 80°C for 1 hour. PH gradually decreases to approx.
Drops to 10. The product, approximately 40% concentrated, became cloudy after 2 days at room temperature.
2.1.2
実施例1.2で得た生成物80ｇ（0.32モル、
Ntitrから算出）を水134ｇに分散させ、新た
に調製した40％クロル酢酸ナトリウム溶液
214ｇ（0.74モル）を60℃で混合する。次い
で、60℃で50％苛性ソーダ溶液58.8ｇ（0.74
モル）を加え、混合物を60℃で２時間保つた
後、80℃に加温する。苛性ソーダ液を加えて
PHを11.5に調節し、80℃で１時間加熱すると
10.1に下がる。2.1.2 80 g of the product obtained in Example 1.2 (0.32 mol,
Freshly prepared 40% sodium chloroacetate solution by dispersing (calculated from Ntitr) in 134 g of water.
214 g (0.74 mol) are mixed at 60°C. Then, 58.8g (0.74g) of 50% caustic soda solution at 60℃
mol) is added and the mixture is kept at 60°C for 2 hours and then warmed to 80°C. Add caustic soda solution
Adjust the pH to 11.5 and heat at 80℃ for 1 hour.
It drops to 10.1.
固型分含量約40％の透明溶液を得るが、こ
れは室温で２日後に濁り始めた。 A clear solution with a solids content of about 40% was obtained, which became cloudy after 2 days at room temperature.
2.1.3
実施例1.3で得たイミダゾリン90ｇ（0.3モ
ル）を水134ｇに分散し、60℃で１時間保つ
た後、新たに調製した40％クロル酢酸ナトリ
ウム溶液203ｇ（0.7モル）を加える。次い
で、50％苛性ソーダ液56ｇ（0.7モル）を加
える。PHは11.6に上昇する。この温度で２時
間、さらに80℃で１時間撹拌する。室温で約
10週間貯蔵すると最初の濁りが生じた。2.1.3 90 g (0.3 mol) of the imidazoline obtained in Example 1.3 are dispersed in 134 g of water and kept at 60° C. for 1 hour before adding 203 g (0.7 mol) of a freshly prepared 40% sodium chloroacetate solution. Next, 56 g (0.7 mol) of 50% caustic soda solution is added. PH rises to 11.6. Stir at this temperature for 2 hours and then at 80°C for 1 hour. Approximately at room temperature
After 10 weeks of storage, the first turbidity appeared.
2.2 アルカリ前処理有り
2.2.1
(a) ジアミド0.035モルを含む実施例1.1で得
た生成物90ｇ（0.3モル、Ntitrから算出）
を水148ｇに分散させ、50％NaOH1.2ｇ
（0.015モル）を加えた後、80〜90℃で１時
間撹拌する。次いで2.1.1に記載の手順を
繰り返す。2.2 With alkaline pretreatment 2.2.1 (a) 90 g of the product obtained in Example 1.1 containing 0.035 mol of diamide (0.3 mol, calculated from Ntitr)
Dispersed in 148g of water, 1.2g of 50% NaOH
(0.015 mol) and stirred at 80-90°C for 1 hour. Then repeat the procedure described in 2.1.1.
生成物は、2.1.1の場合と同様に透明で
あるが、全ジアミドがケン化されてはいな
かつたので、６日後には濁り始めた。 The product was clear as in 2.1.1, but became cloudy after 6 days as not all the diamide had been saponified.
(b) 50％NaOH4.8ｇ（0.06モル）を加えて
実験を繰り返した。 (b) The experiment was repeated with the addition of 4.8 g (0.06 mol) of 50% NaOH.
分析により示される様に、ジアミドは定
量的にモノアシル生成物にケン化されたの
で、生成物は６月以上も透明である。 As shown by analysis, the diamide was quantitatively saponified to the monoacyl product so that the product remains clear for more than 6 months.
2.2.2
実施例1.2で得た生成物80ｇ（0.32モル）
を水60ｇに分散させ、50％苛性ソーダ液4.8
ｇ（0.06モル）を加えた後、80℃で１時間撹
拌する。2.2.2 80 g (0.32 mol) of the product obtained in Example 1.2
Dispersed in 60g of water, 50% caustic soda solution 4.8
g (0.06 mol) and stirred at 80°C for 1 hour.
2.1.2に記載の様にさらに反応させた後、
界面活性剤を得たが、これは６月以上も透明
である。 After further reaction as described in 2.1.2,
A surfactant was obtained which remains transparent for more than 6 months.
2.1.1〜2.1.3および2.2.1ならびに2.2.2から次の
ことが明らかである：
品質の改良は、前段階（2.1.3）の様に非常に
純度の高いイミダゾリンを用いたとしても、ジア
ミドを多く含む粗生成物（1.1および1.2）をアル
カリ前処理に付した場合に達成された様には達成
されない。苛性ソーダの使用量は、ジアミド含量
に対して当量または好ましくは約２倍量が有利で
ある。 From 2.1.1 to 2.1.3 and 2.2.1 and 2.2.2 it is clear that: The quality improvement does not occur even when using very pure imidazoline as in the previous step (2.1.3). , is not achieved as was achieved when the diamide-rich crude products (1.1 and 1.2) were subjected to alkaline pretreatment. The amount of caustic soda used is advantageously equivalent to or preferably about twice the diamide content.
実施例 ３
２−アクリルアミド−２−メチルプロパンスル
ホン酸（AMPS）またはNa塩との反応：−
3.1 アルカリ前処理無し
実施例1.2で得た生成物75.0ｇ（0.3モル、
Ntitrから算出）を水200ｇに分散させ、
AMPS80.6ｇ（0.39モル）を、次いで50％苛性
ソーダ液31.2ｇ（0.39モル）を加える。80℃で
４時間撹拌する。Example 3 Reaction with 2-acrylamido-2-methylpropanesulfonic acid (AMPS) or Na salt: - 3.1 Without alkaline pretreatment 75.0 g of the product obtained in Example 1.2 (0.3 mol,
(calculated from Ntitr) in 200g of water,
80.6 g (0.39 mol) of AMPS is added followed by 31.2 g (0.39 mol) of 50% caustic soda solution. Stir at 80°C for 4 hours.
得られた生成物は透明で希薄溶液状である
が、２日後には分離した。 The resulting product was a clear, dilute solution that separated after two days.
3.2 アルカリ前処理有り
実施例1.2で得た生成物75.0ｇ（0.3モル）を
水200ｇに分離させ、50％苛性ソーダ液4.8ｇ
（0.06モル）を加えて80〜90℃で１時間撹拌す
る。さらに、3.1と同様に反応を行う。生成物
は６月以上も完全に透明である。3.2 With alkaline pretreatment 75.0 g (0.3 mol) of the product obtained in Example 1.2 was separated in 200 g of water, and 4.8 g of 50% caustic soda solution was added.
(0.06 mol) and stirred at 80-90°C for 1 hour. Furthermore, carry out the reaction in the same manner as in 3.1. The product remains completely transparent for more than 6 months.
実施例 ４
クロルヒドロキシプロパンスルホン酸または
Na塩との反応：−
4.1 アルカリ前処理無し
実施例1.2で得た生成物75ｇ（0.3モル）を水
200mlに分散させ、クロルヒドロキシプロパン
スルホン（Na塩）63.6ｇ（0.3モル）を加え、
次いで80℃で30分間にわたり50％苛性ソーダ液
24.0ｇ（0.3モル）を加える。50℃で４時間反
応させる。Example 4 Chlorohydroxypropanesulfonic acid or
Reaction with Na salt: − 4.1 Without alkali pretreatment 75 g (0.3 mol) of the product obtained in Example 1.2 was added to water.
Disperse in 200ml, add 63.6g (0.3mol) of chlorohydroxypropanesulfone (Na salt),
Then 50% caustic soda solution for 30 min at 80°C
Add 24.0g (0.3 mol). React at 50°C for 4 hours.
最終生成物は透明であるが、３日後に濁つ
た。 The final product was clear but became cloudy after 3 days.
4.2 アルカリ前処理有り
50％苛性ソーダ液4.8ｇ（0.06モル）を加え
た後にクロルヒドロキシプロパンスルホン酸
（Na塩）を加えて80〜90℃で１時間撹拌する以
外は4.1と同様の反応を行う。4.2 With alkaline pretreatment Carry out the same reaction as in 4.1 except that after adding 4.8 g (0.06 mol) of 50% caustic soda solution, chlorohydroxypropanesulfonic acid (Na salt) is added and stirred at 80 to 90°C for 1 hour.
生成物は６月以上後でも透明である。 The product remains clear even after 6 months or more.
実施例 ５
アクリル酸との反応：−
5.1 アルカリ前処理無し
実施例1.1で得た生成物75.0ｇ（0.3モル）を
アクリル酸21.6ｇ（0.3モル）と混合し、80℃
で４時間撹拌した後、水145ｇで希釈する。生
成物は２週間後に濁つた。Example 5 Reaction with acrylic acid: - 5.1 Without alkali pretreatment 75.0 g (0.3 mol) of the product obtained in Example 1.1 was mixed with 21.6 g (0.3 mol) of acrylic acid and heated at 80°C.
After stirring for 4 hours, dilute with 145 g of water. The product became cloudy after two weeks.
5.2 アルカリ前処理有り
実施例1.1で得た生成物75.0ｇ（0.3モル）を
50％苛性ソーダ液4.8ｇ（0.06モル）と共に80
℃で１時間撹拌し、次いで5.1と同様に更に処
理した。5.2 With alkaline pretreatment 75.0 g (0.3 mol) of the product obtained in Example 1.1 was
80 with 4.8 g (0.06 mol) of 50% caustic soda solution
Stirred for 1 hour at 0.degree. C. and then further processed as in 5.1.
生成物は６月以上も透明を保つ。 The product remains clear for more than six months.
Claims (1)
を表す。］ で示されるアミノアルキルアルカノールアミンと
炭素数６〜22の脂肪酸とのイミダゾリン粗縮合物
を精製し、次いで、精製された縮合物をアルキル
化および要すれば第四級化して貯蔵安定性の高い
両性界面活性剤を製造する方法であつて、脂肪酸
とアミノアルキルアルカノールアミンとの粗縮合
物を、アルキル化の前にアルカリ加水分解に付す
ことにより、該粗縮合物中に存在する一般式： ［式中、ｍおよびｎは前記と同意義である。］ で示されるジアミドから成る副生成物を分解する
ことによつて精製することを特徴とし、前記アル
カリ加水分解において、ジアミドに対して約１〜
３倍モル量のアルカリを使用する方法。 ２ アルカリ加水分解時に加えるアルカリ量を粗
縮合物中に存在するジアミドの量に応じて調節
し、その際好ましくは少くともほぼ等モル量、か
つ約２倍モル量を越えない様にする特許請求の範
囲第１項記載の方法。 ３ アルカリ加水分解処理を約70〜100℃、好ま
しくは80〜90℃の温度で行う特許請求の範囲第１
項または第２項記載の方法。 ４ ｍが２、３または６およびｎが２である前記
一般式で示されるアミノアルキルアルカノールア
ミンを用いる特許請求の範囲第１〜３項のいずれ
かに記載の方法。 ５ 炭素数８〜18の純脂肪酸または任意の脂肪酸
混合物を用いる特許請求の範囲第１〜４項のいず
れかに記載の方法。[Claims] 1 General formula: H 2 N-(CH 2 )m-NH-(CH 2 )n-OH [wherein m represents a number of 2 to 6, and n represents a number of 2 or 3. ] The imidazoline crude condensate of the aminoalkyl alkanolamine represented by the formula and a fatty acid having 6 to 22 carbon atoms is purified, and the purified condensate is then alkylated and, if necessary, quaternized to obtain a product with high storage stability. A method for producing an amphoteric surfactant, which comprises subjecting a crude condensate of a fatty acid and an aminoalkyl alkanolamine to alkaline hydrolysis before alkylation, thereby obtaining the general formula present in the crude condensate: [In the formula, m and n have the same meanings as above. ] Purification is carried out by decomposing a by-product consisting of diamide represented by
A method using three times the molar amount of alkali. 2. A patent claim in which the amount of alkali added during alkaline hydrolysis is adjusted according to the amount of diamide present in the crude condensate, preferably at least approximately the same molar amount and not exceeding about twice the molar amount. The method described in item 1. 3. Claim 1 in which the alkaline hydrolysis treatment is carried out at a temperature of about 70 to 100°C, preferably 80 to 90°C.
or the method described in paragraph 2. 4. The method according to any one of claims 1 to 3, using an aminoalkyl alkanolamine represented by the above general formula in which m is 2, 3 or 6 and n is 2. 5. The method according to any one of claims 1 to 4, using a pure fatty acid having 8 to 18 carbon atoms or any fatty acid mixture.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803018201 DE3018201A1 (en) | 1980-05-13 | 1980-05-13 | METHOD FOR REFINING THE RAW CONDENSATION PRODUCT FROM AMINOALKYLALKANOLAMINES AND FATTY ACIDS, AND IF NECESSARY FOR THE FOLLOWING DETERMINATION OF AMPHOTENSIDE WITH INCREASED STORAGE STABILITY |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5716846A JPS5716846A (en) | 1982-01-28 |
| JPH0249299B2 true JPH0249299B2 (en) | 1990-10-29 |
Family
ID=6102253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7284281A Granted JPS5716846A (en) | 1980-05-13 | 1981-05-13 | Purification of crude condensate of aminoalkylalkanolamine and fatty acid and manufacture of storage-stable amphoteric surfactant |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0040346B1 (en) |
| JP (1) | JPS5716846A (en) |
| AT (1) | ATE5815T1 (en) |
| AU (1) | AU541532B2 (en) |
| BR (1) | BR8102948A (en) |
| CA (1) | CA1214778A (en) |
| DE (2) | DE3018201A1 (en) |
| ES (1) | ES8203830A1 (en) |
| MX (1) | MX156685A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3444864A1 (en) * | 1984-12-08 | 1986-06-12 | Henkel KGaA, 4000 Düsseldorf | METHOD FOR GREATING LEATHER AND FURS |
| DE3641871A1 (en) * | 1986-12-08 | 1988-06-09 | Henkel Kgaa | METHOD FOR THE PRODUCTION OF LIQUID AMPHOTENSIDE |
| DE4038983A1 (en) * | 1990-12-06 | 1992-06-11 | Henkel Kgaa | METHOD FOR THE PRODUCTION OF FLUID-LIQUID IMIDAZOLINIUM TENSIDES BY QUATERNATION OF 1-HYDROXYETHYL-2-ALKYLIMIDAZOLINES |
| DE4240154A1 (en) * | 1992-11-30 | 1994-06-01 | Henkel Kgaa | Process for the production of low viscosity, storage stable amphoteric surfactants |
| CA2132289A1 (en) * | 1993-10-12 | 1995-04-13 | Bharat Desai | Higher purity imidazoline based amphoacetate surfactants and processes for the preparation thereof |
| DE19715383A1 (en) * | 1997-04-14 | 1998-10-15 | Clariant Gmbh | Amphoglycinates as anti-corrosion agents for ferrous and non-ferrous metals |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5289611A (en) * | 1976-01-20 | 1977-07-27 | Lion Corp | Preparation of quaternary ammonium salts |
| JPS5331618A (en) * | 1976-09-03 | 1978-03-25 | Kawaken Fine Chem Co Ltd | Novel amino amide compounds, their preparation and surface-active agents containing the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5368721A (en) * | 1976-12-01 | 1978-06-19 | Lion Corp | Disubstd. aliphatic carboxylic acid amide amines, and detergents and cosmeticcompositions containing the same |
| CA1117137A (en) * | 1977-08-18 | 1982-01-26 | Brinley M. Phillips | Organic nitrogen-containing compounds |
-
1980
- 1980-05-13 DE DE19803018201 patent/DE3018201A1/en not_active Withdrawn
-
1981
- 1981-05-02 EP EP81103328A patent/EP0040346B1/en not_active Expired
- 1981-05-02 DE DE8181103328T patent/DE3161875D1/en not_active Expired
- 1981-05-02 AT AT81103328T patent/ATE5815T1/en not_active IP Right Cessation
- 1981-05-11 CA CA000377290A patent/CA1214778A/en not_active Expired
- 1981-05-12 ES ES502137A patent/ES8203830A1/en not_active Expired
- 1981-05-12 BR BR8102948A patent/BR8102948A/en not_active IP Right Cessation
- 1981-05-13 AU AU70511/81A patent/AU541532B2/en not_active Ceased
- 1981-05-13 JP JP7284281A patent/JPS5716846A/en active Granted
- 1981-05-13 MX MX187279A patent/MX156685A/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5289611A (en) * | 1976-01-20 | 1977-07-27 | Lion Corp | Preparation of quaternary ammonium salts |
| JPS5331618A (en) * | 1976-09-03 | 1978-03-25 | Kawaken Fine Chem Co Ltd | Novel amino amide compounds, their preparation and surface-active agents containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0040346A1 (en) | 1981-11-25 |
| AU7051181A (en) | 1981-11-19 |
| JPS5716846A (en) | 1982-01-28 |
| ATE5815T1 (en) | 1984-01-15 |
| AU541532B2 (en) | 1985-01-10 |
| EP0040346B1 (en) | 1984-01-11 |
| BR8102948A (en) | 1982-02-02 |
| CA1214778A (en) | 1986-12-02 |
| DE3018201A1 (en) | 1981-11-19 |
| ES502137A0 (en) | 1982-04-01 |
| ES8203830A1 (en) | 1982-04-01 |
| MX156685A (en) | 1988-09-26 |
| DE3161875D1 (en) | 1984-02-16 |
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